14526-03-5

Basic information

• Product Name: CHLOROACETATE
• Synonyms: CHLOROACETATE
• CAS NO: 14526-03-5
• Molecular Formula: C₂H₂ClO₂
• Molecular Weight: 93.48908
• Mol File: 14526-03-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CHLOROACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROACETATE(14526-03-5)
• EPA Substance Registry System: CHLOROACETATE(14526-03-5)

Safety Data

• Hazardous Substances Data: 14526-03-5(Hazardous Substances Data)

Usage

General Description

Chloroacetate refers to a group of organic compounds derived from acetic acid in which one or more hydrogen atoms are substituted with chlorine atoms. These compounds are commonly used as intermediates in the production of various chemicals, including pharmaceuticals, herbicides, and insecticides. Chloroacetate compounds are highly reactive, and their reactivity can vary depending on the specific structure of the compound. They are often used in chemical reactions to introduce the chloroacetyl functional group into organic molecules, and their properties make them valuable building blocks in organic synthesis. However, due to their high reactivity and toxic nature, chloroacetate compounds require careful handling and disposal to prevent adverse effects on the environment and human health.

Upstream product

• 1163712-05-7 C₇H₁₁BP^(1-) 
• 79-11-8 chloroacetic acid 
• 14357-05-2 2,2,2-trichloroacetate 
• 13425-80-4 dichloroacetate ion 
• 1580541-42-9 4,4'-dimethoxybenzhydryl chloroacetate 
• 1580541-41-8 4-methoxy-4'-phenoxybenzhydryl chloroacetate 
• 1580541-40-7 4-methoxy-4'-methylbenzhydryl chloroacetate 
• 1580541-39-4 4-methoxybenzhydryl chloroacetate 
• 188819-30-9 C₂H₄NO₃^(1-) 
• 184582-82-9 C₃H₆NO₄^(1-) 
• 96-34-4 methyl chloroacetate 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 16887-00-6 chloride 
• 79-11-8 chloroacetic acid 
• 1163712-05-7 C₇H₁₁BP^(1-) 
• 79-14-1 glycolic Acid 
• 184582-82-9 C₃H₆NO₄^(1-) 
• 188819-30-9 C₂H₄NO₃^(1-) 
• 115859-54-6 4-[3-Eth-(Z)-ylidene-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 126083-71-4 (2,2',4,4',6,6'-hexanitro-diphenyl)-methyl anion 
• 126083-72-5 C₁₃H₆N₅O₁₀^(1-) 
• 27610-20-4 substituted benzenethiol 
• 4382-72-3 methoxymethyl chloroacetate 

Relevant articles and documents

How the sustainable solvent water unleashes the photoredox catalytic potential of ruthenium polypyridyl complexes for pinacol couplings

By complementing laser flash photolysis with product studies in visible-LED driven syntheses, we show that the one-electron reduced forms OER of tris(2,2′-bipyridine)ruthenium(ii) and its more reactive derivative with 4,4′-dimethylated ligands exhibit a reductive power greater by 0.2 eV in water than in acetonitrile; and that this difference allows the reduction of carbonyl compounds, and thus pinacol couplings, in aqueous medium via ruthenium-based photoredox catalysis as an alternative to using more expensive and less photostable higher-energy complexes (e.g., of iridium). Ascorbate serves as sacrificial donor to access OER. SDS micelles or cyclodextrins as carriers help overcome solubility problems of less hydrophilic substrates, and more reactive water-soluble substrates can even be coupled at neutral pH, such that the mild conditions make the process fully sustainable.

The Ever-surprising chemistry of boron: Enhanced acidity of phosphine·boranes

The gas-phase acidity of a series of phosphines and their corresponding phosphine·borane derivatives was measured by FT-ICR techniques. BH 3 attachment leads to a substantial increase of the intrinsic acidity of the system (from 80 to 110 kJ mol-1). This acidity-enhancing effect of BH3 is enormous, between 13 and 18 orders of magnitude in terms of ionization constants. This indicates that the enhancement of the acidity of protic acids by Lewis acids usually observed in solution also occurs in the gas phase. High- level DFT calculations reveal that this acidity enhancement is essentially due to stronger stabilization of the anion with respect to the neutral species on BH3 association, due to a stronger electron donor ability of P in the anion and better dispersion of the negative charge in the system when the BH3 group is present. Our study also shows that deprotonation of ClCH2PH2 and ClCH 2PH2·BH3 is followed by chloride departure. For the latter compound deprotonation at the BH3 group is found to be more favorable than PH2 deprotonation, and the subsequent loss of Cl- is kinetically favored with respect to loss of Cl - in a typical SN2 process. Hence, ClCH2PH 2·BH3 is the only phosphine·borane adduct included in this study which behaves as a boron acid rather than as a phosphorus acid.

Structure-Activity Relationships in the Esterase-catalysed Hydrolysis and Transesterification of Esters and Lactones

The Broensted exponents for the alkaline hydrolysis of alkyl esters are 1.3 and 0.4 for substitution in the acyl and alcohol portions, respectively, which is indicative of a transition state which resembles the anionic tetrahedral intermediate with a localised negative charge.By contrast, the rate of the pig liver esterase (PLE)-catalysed hydrolysis shows little dependence upon the electron-withdrawing power of substituents.The values of kcat are independent of the pKa of the leaving group alcohol suggesting rate-limiting deacylation.There is a small steric effect of α-substitution in both the alcohol and carboxylic acid residues for the enzyme-catalysed reactions but the enzyme rate enhancement factor remains high for most esters.There is no substantial ee observed for the hydrolysis of racemic esters although the kinetic data can be used for determining the regioselective hydrolysis of diesters.Unsubstituted lactones are poor substrates for PLE but derivatives with hydrophobic substituents show kcat/Km values similar to those for acyclic esters.Dihydrocoumarin undergoes transesterification catalysed by PLE, kcat increases with increasing alcohol concentration indicative of rate-limiting deacylation.There is enantioselectivity in the PLE-catalysed hydrolysis of some racemic lactones but little or none in the transesterification of racemic alcohols with dihydrocoumarin.